The tradition of chalk art on pavement began in 16th century Italy where drifting artists traveled between festivals living off coins thrown by their drawings. Today there are between 50 to 100 chalk festivals in the U.S. annually, including this weekend's street fair in Kennebunkport, Sept 23-24. Here's the schedule and slideshows from 2017, 2018  & 2019 to pique your curiosity.

Text: Town of Kennebunkport's "Chalk Art History" (watch the free documentary)  Image:  Carol Cook and Katahdin

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 Free (& Cheap) Events 

September 22-28, 2022

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Thursday, September 22

Free Moose Hunting Trip for a Purple Heart Vet (Sept 24-Oct 2)

Give Input to Improve Regional Transit, 8 am-4 pm, 3 Locations, Portland

Craft & Chat for Ages 50+ (weekly), 9-11 am, Community Ctr., South Portland

Age-Friendly Guided Walk, 10 am, Simpson's Woods, Freeport

Watch the Maine Senior Games- Candlepin Bowling, 10 am, Big 20, Scarborough

Local Hikes for Ages 50+, 10 am-12 pm, Falmouth

Farmington Fair $5 Admission Ages 62+, 12-7 pm, Farmington

Walk with a Doc, 12:15-12:45 pm, Wellness Wy., Topsham

People Plus Open House, 1-3 pm, Union St., Brunswick

Theater: Sun Universe, 2-2:45 pm, School St., Brunswick

Artist talk: Paula Gerstenblatt, 2-4 pm, Jewish Museum, Portland

Senior College- Aging, Health & Happiness, 2-4 pm, Library, Auburn

Whiskey Worth Knowing & Engraving (tasting), 4-6 pm, Man & Oak, Portland

Talk & Reception: Thinking about Migration through Latinx Art, 4:30-7 pm, Bowdoin, Brunswick

Wine Tasting, 5-7 pm, Vessel & Vine, Brunswick

BIPOC Business After Hours, 5:30-7:30 pm, Washington Ave., Portland

Community Spokes Bicycle Advocate Training, 5:30-7:30 pm, Portland

Meetup, Active Singles 40-60s- Trivia Night, 5:30-7:30 pm, Flight Deck, Brunswick

BYO Crafts Senior Drop In (Th weekly), 5:30-8 pm, Senior Ctr., Auburn

Monthly Dinner for Older LGBTQ+ Adults ($0-8), 6 pm, Portland

City Climate Action Plan Public Workshop, 6:30 pm, Town Hall, Falmouth

Movie: Running Home (doc), 6:30 pm, The Point, South Portland

Teen Game Night, 6:30-8 pm, Library, Cumberland

The Playful Process of Song Making Workshop ($0+), 6:30-8:30 pm, Greenwood Garden, Peaks Island

Movie: Belfast, 6:45-8:30 pm, Library, Kennebunkport

Bike Bidd/Saco Lights & Music Bike Ride, 7-9 pm, Main St., Biddeford

Outdoor movie: Wreck-It Ralph, 7-9 pm, Nonantum, Kennebunkport

Outdoor movie: Outdoor Film Festival Shorts ($0-10), 7 pm, Pearl St. Garage, Biddeford

Tonight's Cheap Night Life

Virtual Events

Funding Your Business, 12 pm

Freezing Fruits & Vegetables, 12-12:45 pm

Preserving the Maine Harvest Workshop ($0-5), 12-12:45 pm

Holiday Prep- Social Media Marketing, 12-1 pm

Credit Score Improvement Seminar, 5:30-6 pm

Join the Youth Voting Network, 5:30-6:30 pm

Leveraging Your Power with the Maine Women's Lobby, 6-7:30 pm

Stars Over Katahdin 2022- Astronomy Talks, 6:30-8 pm

Meetup, Acoustic Guitar Jam, 6:30-8:30 pm

Meditation with Melissa Boyd (hybrid; $0+), 7 pm



Friday, September 23

Common Ground Fair Free for Disabled, Under 12 & Volunteers (9/23-25), Unity

$3 Furniture Fridays at Goodwill (ends Sept 30)

Overdose Recognition, Narcan & CPR Training, 7:30-8:30 am, Vets Center, Windham

Free Book & Puzzle Swap (M-F all year), 8 am-4:30 pm, Town Hall, Kennebunk

Maine State Championships All Breed Horse Show (9/23-25), 8 am-night, Fairgrounds, Skowhegan

Crop Cover Volunteer Day, 9-11 am, Hacker's Hill, Casco

Volunteer Work Day at Tear Cap Workshops, 9-12 pm & 1-4 pm, Hiram

Chalk the Port, 9 am-4 pm, Recreation Way, Kennebunkport

Games & Gather for Ages 55+ (Tu,F weekly), 10 am-2 pm, Hub, Scarborough

Meetup, Maine Women in Tech, 10 am-2 pm, Rwanda Bean, Portland

Animal Ambassador Visit, 12-2 pm, Maine Beer Co., Freeport

Bio365 Biochar Soil Launch + Swag, 12-4 pm, HTG Supply, Portland

Northpoint Mortgage Ribbon Cutting + Food, 12-4 pm, Rt. 1, Falmouth

Music: New Relm, 2 & 7 pm, Sawyer Rd., Greene

Author talk: Memoirs of an Amish Childhood, 2-3:30 pm, Library, Lewiston

LGBTQIA + Allies Teen Hangout, 2:30-4 pm, Library, Cumberland

Champlain French Film Festival, 4 pm, USM, Portland

Community Yoga Class ($0+), 4:30-5:30 pm, The Daily Sweat, Kennebunk

CornerFEST, 4:30-7:30 pm, Woodford St., Portland

Queer Makers Night Market, 5-9 pm, Congress Sq. Park, Portland

Youth Advisory Board Meeting (ages 11-13), 5:30 pm, Hub, Scarborough

Variety Open Mic Coffee House, 6 pm, River Rd., Windham

Reiki Session, 6-7 pm, Library, Raymond

Trails in the Valley Run Club (weekly), 6-7 pm, Lost Valley, Auburn

Music: Concert for Huot House Homeless Vets ($0-5), 6-8 pm, Grange 53, Saco

21+ Karaoke Night, 6-10 pm, Roosevelt Trl., Windham

Dempsey Challenge's "A Night of Love + Light", 6:30-8 pm, Simard-Payne Park, Lewiston

Music: Genticorum ($0-20), 6:30-8 pm, Church Ave., Peaks Island

Music: BasementBangerz (ages 16+), 7-10 pm, Main St., Sanford

Music: 4 Bands, "A Night of Horrific Noise" ($0-10), 8 pm, Apohadion, Portland

Tonight's Cheap Night Life


Saturday, September 24

Free Admission to All National Parks

12 Farmers' Markets Today> Here's the Weekly Schedule

Marsh Bird Walk, 8-9:30 am, Blue Point Preserve, Scarborough

Document Shredding + Canned Food Drive, 8 am-12 pm, Saco & Bidd Savings, Biddeford

Nerdcamp Literary Un-Conference, 8 am-3:30 pm, USM, Gorham

Scent Work AKC Dog Show, 8 am-6 pm, Robie School, Gorham

Chalk the Port + Live Music, 8 am-7 pm, Recreation Way, Kennebunkport

Maine State Championships All Breed Horse Show, 8 am-night, Fairgrounds, Skowhegan

September Volunteer Work Party, 9-11 am, Turkey Hill Farm, Cape Elizabeth

Last of Season Makers Market, 9 am-4 pm, Ossipee Trl, Standish

Kids Bike Ride Race (ages 5-12), 9:15 am, Arundel

Champlain French Film Festival, 10 am, 2, 4, 6 pm, USM, Portland

Clark's Pond Trail Ribbon Cutting, 10-10:30 am, South Portland

Fall Trail Clean Up Day, 10 am-12 pm, Clifford Park, Biddeford

Urban Foraging with Rewild Maine, 10 am-12 pm, Town Hall Trailhead, Cumberland

Repair Cafe (repair items to reduce waste), 10 am-12:30 pm, Library, Brunswick

Mock SAT Exam, 10 am-1 pm, Library, Falmouth

Listen to/Join the All-Ages Drum & Bugle Corp, 10 am-2 pm, Broadway, South Portland

Pollinator Bioblitz, 10 am-2 pm, 3 parks, South Portland

Veterans & Family Outdoor Expo, 10 am-2 pm, Cabela's, Scarborough

23rd Apple Pumpkin Festival, 10 am-3 pm, Rec Fields, Livermore Falls

Harvest Fair- Petting Zoo, Kid Stuff, 10 am-3 pm, St. Brigid, Portland

Shaker Museum Apple Festival, 10 am-4 pm, Alfred

Mountain Bike Social & Group Ride ($0-20), 10:30 am, Industrial Wy., Portland

Kids Carnival (followed by free football game), 11 am-1 pm, Bates, Lewiston

Cahoots- Art, Community, Music, Free Pizza, 11 am-2 pm, McKeen St., Brunswick

Artisan Fair, 11 am-4 pm, Wallingford's Fruit House, Auburn

Fall Fest 2022, 11 am-4 pm, Veteran's Park, Old Orchard

Free Subs & Soda, 11:30 am, Big Moose Harley, Portland

American Shaman CBD Ribbon Cutting, 12-2 pm, Maine St., Brunswick

Outdoor music + Historical Grocery Open House, 12-3 pm, Windham Ctr. Rd., Windham

New Story Walk + Food, Lawn Games, 1-2 pm, Community Ctr., North Yarmouth

Clean Elections Sign Making Party + Cider, Donuts, 1-3 pm, Payson Park, Portland

Open Bench Project Space Tour, 1-3 pm, Congress St., Portland

Androscoggin Co. Fish & Game Open House, 1-4 pm, Perkins Ridge Rd., Auburn

Old Fashioned Games & Open House, 1-4 pm, Knight House, Auburn

Youth in Recovery Fall Field Games Day, 1-5 pm, Bishop St., Portland

Steven King Trivia Time, 1:30-2:30 pm, Library, Gray

Meetup, Portland by Night- Apple Picking, 2-4 pm, Randall Orchards, Standish

Self Defense Class for Immigrant Women, 3-5 pm, TBD, Portland

Mid-Autumn Moon Festival Potluck, 3-6 pm, Ft. Williams, Cape Elizabeth

Dimensions in Jazz Workshop, 4-5:30 pm, Neal St., Portland

September Frith Farm Tour ($0-20), 4-6 pm, Scarborough

Meetup, Russian Portland, 5-7 pm, Portland

Longfellow Park's 95th + Salsa Dancing, Music, 5-8:30 pm, Portland

Watch/Join Maine Mayhem Women's Football Tryouts, 5:30 pm, Ludlow St., Portland

Drum Circle ($0+), 6-7:30 pm, Flourish, Biddeford

Outdoor music: American Ride, 6-9 pm, Main St., Bridgton

Nautical Star Party with Maine's First Ship, 6-9 pm, Commercial St., Bath

Twilight in the Park- Luminarias for Deceased, 6:30 pm, Deering Oaks, Portland

Tonight's Cheap Night Life


Sunday, September 25

Cumberland Fair Free for Wheelchairs & Kids <12 (9/25-10/1), Cumberland

Maine State Championships All Breed Horse Show, 7:30 am-end, Fairgrounds, Skowhegan

Audubon Field Trip- Androscoggin River Trail, 8-11:30 am, Lisbon

Meetup, Join a 6-Man Rowboat Crew (weekly), 8:30-10 am, Lake Auburn, Auburn

Cars & Coffee, 9 am, MacDonald Motors, Bridgton

Free Photo Session with Kids/Adult Dresses, 9 am-2:45 pm, Ft. Williams, Cape Elizabeth

The Impact of Mindset, Mental Toughness & Attitude, 10-11 am, H2O Fitness, Scarborough

Matchless Firestarting & Campfire Safety, 10-11:30 am, Sheridan St., Portland

Electrify Freeport Clean Energy Expo, 10 am-2 pm, High School, Freeport

Shaker Museum Apple Festival, 10 am-4 pm, Alfred

Free Apple Picking for SMCC Family & Friends, 10 am-6 pm, Orchard Ridge, Gorham

Queer Makers Market, 11 am-3 pm, Congress Sq. Park, Portland

Artisan Fair, 11 am-4 pm, Wallingford's Fruit House, Auburn

Watch Medieval Knights Practice Fighting, 12 pm, W. Auburn Rd., Auburn

End of Season Car Show + Country Band, 12-5 pm, Bentley's, Arundel

Board Games at Historic Schoolhouse, 1-4 pm, Boothby St., Auburn

Hang with Infinite Kindness Project (nurse burnout), 2:30-4:30 pm, Chebeague Isl.

Author talk: Phuc Tran, Sigh Gone ($0+), 3 pm, Arts Center, Denmark

Music: Resonant Rogues, 3-5 pm, Maine Craft, Portland

Paws & Read with Therapy Dogs, 3:30-4:30 pm, Library, Freeport

Explore Tarbox Preserve, 4:30-6 pm, Topsham

Community Kirtan ($0-15), 6-7:30 pm, Flourish, Biddeford

Meetup, Book Lovers Reading & Literacy Group, 6-7:30 pm, Panera, South Portland

Outdoor movie: The General (silent), 6:30-8 pm, Congress Sq. Park, Portland

Tonight's Cheap Night Life


Monday, September 26

Cumberland Fair- $5 Day for Military/Vets; Homeschool/Day Care Free, 6 am-7 pm, Cumberland

Age-Friendly Yoga (weekly), 9:30 am, Community Ctr., Freeport

Seniors: The Nature of Fall, 10-11 am, Senior Ctr., South Portland

Amish Star Hot Pad Class, 10 am-12 pm, Community Ctr., Falmouth

Rosh Hashanah + Potluck, 10 am-1 pm, Main St., Ogunquit

Learn More About Medicare, 10:30-11:30 am, Library, Topsham

Cards for Ages 50+ (M,Th weekly), 12-3 pm, Community Ctr., South Portland

Let's Talk About Hospice, 1 pm, Library, Scarborough

Shofar in the Park (Rosh Hashanah), 4:30-5 pm, Ft. Allen, Portland

Talk: The Bifurcation of America, 5-7:30 pm, UNE, Portland

Yoga on the Hill, 5:30-6:30 pm, Hacker's Hill, Casco

Sign Language Class, 6-7 pm, Library, Windham

Hip Hop in the Park, 6-8 pm, Congress Sq. Park, Portland

Intro to Acting Class, 6-8 pm, call for location, Portland

Talking to Your Kids About Sex, 6-9 pm, Maine Mall Rd., South Portland

Talk: The Mystery of Maine's Wildlife, 7-8 pm, Library, Brunswick

Improv Comedy Incubator (weekly; $0-5), 7-9 pm, Woodfords Club, Portland

Tonight's Cheap Night Life


Tuesday, September 27

Meetup, HIIT Class, 6-6:45 am, Payson Park, Portland

Cumberland Fair- $5 Ages 65+ Today, 7 am-7 pm, Cumberland

L/A ‘Think Local’ Biz Networking (hybrid; weekly), 8:30 am, Lisbon St., Lewiston

Senior Finance- Budgeting & Inflation, 9-10 am, Senior Center, South Portland

Free Admission Tuesday (weekly), 10 am-5 pm, Brick Store Museum, Kennebunk

Walk with a Doc, 12:15-12:45 pm, Maine St., Brunswick

Teen Apple Printing, 3:30-4:30 pm, Library, Kennebunk

Kids Chess Club (weekly), 4-5 pm, Library, Cumberland

Business After Hours Networking, 5-7 pm, Blaze Brewing, Biddeford

Girl Scouts K-3 Sign Up & Activity, 5:30-6:30 pm, Mast Landing, Freeport

Wes McNair Open Air Book Launch, 6-7 pm, Congress Sq. Park, Portland

Ticks- A Proactive Approach, 6:30 pm, Library, Cumberland

Slow Flow New Moon Yoga ($0-20), 7-8 pm, Flourish, Biddeford

Tonight's Cheap Night Life

Virtual Events

Holiday Prep- How to Manage Shipping Costs, 10:30-11:30 am

End of Year Business Tax Planning, 2-3 pm

League of Women Voters Discussion Forum, 6:30-7:30 pm

Talk on Maine Wildlife, 6:30-7:30 pm

Book talk: History of America's Public Lands, 7-8 pm

How Maine’s Warming Winters Affect Our Forests, 7-8:30 pm


Wednesday, September 28

November Project- Maine State Pier Workout, 6:29 am, Portland

Local Business Networking, 8:15-9:45 am, Run of the Mill, Saco

Pondicherry Park Walk, 9-10 am, Bridgton

Bingocize (bingo + exercise; M,W weekly), 10-11 am, Republic Ave., Topsham

Cribbage ($3; weekly), 10 am-12 pm, Town Hall, Buxton

Voter Registration Day, 10 am-1 pm, Library, South Portland

Drop In Group for New Parents (weekly), 12:15-2 pm, Birth Roots, Portland

Get Out! Fungi Nature Walk, 1:30-3 pm, Sam Ristich Trails, North Yarmouth

Seniors- Shopping for a Healthy Heart, 2-3 pm, Senior Ctr., South Portland

Taco Cord Holders Teen Craft, 2:15-7 pm, Library, Freeport

Make Art with Art Van (weekly), 3:30 pm, Library, Lewiston

L/A Business Networking, 4-6 pm, DaVinci's Eatery, Lewiston

New to the Region Networking Night, 5-6:30 pm, Leeds

Discover Downtown Westbrook Open House + Art, 5:30 pm, Main St., Westbrook

Mountain Bike Outing, 5:30-7 pm, Neptune Woods, Brunswick

Ukulele Group, 5:30-7 pm, Library, Kennebunk

Waypoints, a Celebration of Portland Trails, 5:30-7 pm, Congress Sq. Park, Portland

Homebuyers Seminar (+ free pizza), 6 pm, Turner St., Auburn

Your Medicare & Social Security Benefits, 6-7:30 pm, High School, Windham

Indigenous Past & Present- Who Tells the Story?, 6-8 pm, Library, Brunswick

Music: Hippie Brothers Band, 6-9 pm, The Axe Pit, South Portland

Author Talk with Rick Simonds, 6:30 pm, Library, North Gorham

Book talk: The History of Coastal Maine, 6:30 pm, Library, South Portland

Music: Adam Swanson, Pianist & Entertainer ($0-10), 6:30-8 pm, Neal St., Portland

Wednesday Warhammer (weekly), 7-11 pm, Croman Game Ctr., Saco

Tonight's Cheap Night Life

Virtual Events

Learning & Developing Apple Device Skills (Sept 28-Nov 9), 10-11 am

Business Startup Checklist, 1-2 pm

Boat Captain License Info Session, 6-8 pm